Wow: Don Draper has possibly the greatest stroke of advertising genius since The Carousel — that anti-tobacco Times ad is about the ballsiest (professional) thing he's ever done — and all I can think about are hats. In other news, Pete's tie is even skinner than usual, Sally's doing better, Betty is still nuts (great shades, though), and, man, this season has been amazing. Stay tuned for our season style review on Friday, plus live-tweeting and a mega recap for next Sunday's finale.

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Anyway, hats. How do you wear one these days without looking like a schmuck? Or without looking like Don Draper circa 1965, to be perfectly honest? There are so many shapes – fedoras, homburgs, porkpies, flat caps. And we get to see an even larger array in our brother recaps of Boardwalk Empire. As for this day and age? We tend to see the pork pie largely on junky rockers, homburgs on martyred gangster rappers, and all of the above on actual gangsters.

Not so many flat caps and homburgs in '65 – it's fedora or bust for the fellas at Sterling/Cooper/Draper/Pryce. And the fedora is, more or less, universally flattering — provided that it fits, of course. The angle at which you wear it makes perhaps the largest difference. Don wears his hat straight and level – all business. You can push it back for a bit of devil-may-care jauntiness. Or you can pull it down over your eyes for a dark and dramatic look, but beware: the jerk potential is high with a hat these days, now that it's a highly nonessential item. For my money, I would err on the side of jaunty and casual, to keep your lady friends from thinking you have an obsession with Humphrey Bogart.

Now don't get me wrong: Hats are sexy, and I encourage them. But if you decide to partake, do yourself a favor and invest in a high-quality fedora. Don't wince at the price – you really only need one, and if cared for properly it can last you for years. Borsalino is a good place to start for a classic luxury topper, or Eugenia Kim or Paul Smith for more exotic interpretations of the classic shapes. Whatever your pleasure, remember that the classic rules still apply: If you are in an elevator, at dinner, or in the home of another, take off your hat. No need to tip it or anything — just don't be ridiculous. If you're feeling hamstrung by the idea, take a note from Mr. Draper and just plunge in boldly. You may end up producing your best work yet.